They called him the Cobra in Australia, where he played pro basketball for four years. Maybe it was the way he would languidly uncoil his 6-foot-5 frame before striking with his jumper. Not even Arne Duncan himself knows why a “crazy announcer” gave him the nickname—and likely never will: “That guy’s dead.”

The moniker seems wildly ill fitted to the gentle-souled former U.S. secretary of education. Popping blue-and-white Community Trust–branded M&Ms and sipping apple juice in the conference room of the Michigan Avenue high-rise where he keeps an office these days, the sleeves of his crisp blue button-down rolled up and his close-cropped gray hair precisely coiffed, Duncan looks more like the guy who ran the DECA club back in high school than a venomous reptile.

He does share one trait with the cobra, however: It is the only snake that stays with its nest, relentlessly guarding its young until they’re ready to enter the wider world.

When he left President Obama’s cabinet last December, after seven years, Duncan, 51, had no shortage of options. But whatever he did next, one thing was nonnegotiable: It would be in his hometown of Chicago, where he spent his childhood playing pickup basketball and later served as CEO of public schools. After all, the city, his nest, is in crisis. Murders are at a 20-year high, and a staggering 46 percent of black men ages 20 to 24 are both out of work and out of school, according to an often-quoted study by the University of Illinois at Chicago’s Great Cities Institute. 

“Very, very, very naively [before leaving Chicago], I assumed it couldn’t get any worse,” Duncan says. “Coming back, talking to everyone—cops, leaders, guys on the streets—everybody just said, ‘Arne, it’s getting worse. What are you going to do?’ ”

By March he had his answer: He would join forces with the Emerson Collective, a deep-pocketed California- based philanthropic organization headed by Steve Jobs’s widow, to create an ambitious employment program in Chicago targeted at young black men. If they had a legit way to make a decent living, Duncan reasoned, they would be less likely to pick up a gun. And so, this summer, he dived in, putting together a nine-person staff, meeting with potential employers, funding 4,700 summer jobs for high school students, and launching a skills-training course populated mostly with ex-cons. 

“This is a grand bargain,” Duncan explains. “We want you to stop shooting. We want to help you make a living in the legal economy. Many, not all, would make a different set of choices if they had them. It’s the absence of those choices that’s perpetuating so much of the violence.”

Arne Duncan spends a lot of time in Cook County Jail these days. He regularly meets with inmates, 40 to 50 at a time, listening—really listening—to their stories and asking what might have kept them out of trouble. It’s not a new practice. He’s always prided himself on having his ear to the ground. Whenever he visited Chicago while still in the cabinet, he would chat up people on the South Side during neighborhood pickup games and stop by the jail even then. 

“I talked to one young guy. He had done some pretty horrific stuff,” Duncan recalls. “He said, ‘Arne, I just got tired of hearing my mother cry at night, and I couldn’t pay the gas bill, couldn’t pay the electric bill. I had to do what I had to do.’ He knew who he had to talk to on his block to go make some money. And that led him down the path.” The man joined a gang and began dealing drugs.

It wouldn’t take much, Duncan learned, to persuade these men to get off the streets. “I always either start or end here with these guys: ‘What will it take in terms of a job to get you to stop shooting?’ This is the consensus: It’s not unanimous, but it’s like $12.50 an hour, $13, $14 an hour. It’s peanuts.”

Duncan grew up around guys like these, living in Hyde Park and hanging out at his mother’s after-school tutoring program, the Sue Duncan Children’s Center, in the South Side neighborhood of Oakland. “He’s been living life with inner-city urban kids since he was a toddler,” says lifelong friend and Ariel Investments CEO John Rogers Jr., who met Duncan while playing pickup basketball as a kid at the University of Chicago’s Bartlett Gymnasium. (Duncan could play there because his dad was a professor; Rogers admits to sneaking in.) “He’s been in their homes on the evenings when the worst things have happened, when kids have been slain or their mom has overdosed.” 

The environment “shaped all of us,” Duncan says. “These were our friends. They were our extended family—kids who happened to be all black. Happened to be all very poor. Happened to often not have the most functional families. Happened to live in a very violent neighborhood but had this amazing potential.”

A combination of factors over the years has created the heinous economic conditions that permeate much of Chicago’s South and West Sides. The closest jobs were once in factories, but those began disappearing in the ’70s and are virtually absent today. (The state has lost more than 300,000 manufacturing jobs since 2000 alone.) There isn’t nearly enough retail work in the area to compensate, and many of the young people Duncan is targeting don’t have the mobility—access to cars, money for bus fare—to get to the places where the jobs are. Nor, in many cases, do they have the education to qualify for those jobs. Then there are more recent compounding factors: The recession and federal cuts to summer job programs have eliminated opportunities for almost 10,000 Chicago teens. The result is a generation of young South and West Side men with few prospects.

“There’s not a day in my life here that somebody isn’t asking me for a job,” says the Reverend Michael Pfleger, Duncan’s friend and an activist pastor at St. Sabina Catholic Church in the Auburn Gresham neighborhood. “We keep telling young people, ‘Put down the guns, don’t sell drugs,’ and that’s all good. But then you’ve got to sell them something. Because it’s about survival. You put two lions in the cage and don’t feed them, one’s going to die.” 

The response to the increase in violence has been woefully inadequate, Duncan says: “It’s like we’re fighting the AIDS epidemic and we’re acting like it’s the flu.” The problem, he insists, is not something the city can arrest its way out of. “The police have a very important role to play, but the police are always after the fact. It’s about prevention.” It costs about $52,000 to lock up a man in Cook County Jail for a year, Duncan points out. What if that money could go to his salary instead? 

When Duncan returned to Hyde Park after leaving the cabinet, he began talking about these issues with Laurene Powell Jobs, Emerson’s founder, whom he’d gotten to know over the years during panel appearances and conferences. The notoriously private widow of Apple’s founder has a personal net worth of nearly $18 billion and reportedly funnels much of her giving through Emerson. The organization funds a variety of immigration, social justice, and education ventures across the country, such as Project XQ, a $100 million initiative launched last year to crowdsource new approaches to high school.

Emerson prides itself on taking on the toughest challenges, so when Duncan told Powell Jobs he wanted to tackle the dual crises of unemployment and violence in Chicago, she agreed to back him. “I said, ‘This is just really, really hard stuff, and we may fail. I can’t promise you victory is assured,’ ” Duncan recalls. “The fact that this was so hard didn’t scare her. In fact, that was appealing to her.” The organization hasn’t put a price tag on how much money it’s willing to direct to the Chicago initiative. But, says Duncan, “Laurene has committed for the long haul.”

Duncan has never shied away from bold bets. At Chicago Public Schools, he boosted early-childhood programs, aggressively hired new teachers, and took the controversial step of replacing a number of neighborhood schools with charter schools; test scores and graduation rates subsequently rose. As secretary of education, he pushed policies that ruffled feathers on both sides of the aisle, such as the Common Core curriculum standards and teacher evaluations that relied heavily on student performance on standardized tests. Still, there were undeniable victories, like the $1 billion he got redirected toward early-childhood education and the reduction in high school dropout rates by 27 percent during his tenure. (Duncan responds to speculation about a mayoral run by silently shaking his head before offering a curt “No.”)

More than anything, Powell Jobs is wagering on Duncan himself. “Arne is coming at this with a full toolkit of talents,” she says. “He will ask the right questions. He will spend time on community. He will use analysis and empiricism—all the smart tools of understanding. If policies and programs sound good at the macro level but don’t have an effect on a child’s life, he will have no tolerance for it.” 

Duncan’s plan is aggressive: He wants companies across 10 sectors—including health care, hospitality, and technology—to hire from the pool of 22,000 black men ages 17 to 24 who are not employed and not in school. “This is where the crisis is,” Duncan says, adding that he wants to eventually expand the program to a broader demographic. (“We’re in our infancy,” he emphasizes, noting that Emerson doesn’t have a set goal for the number of jobs it wants to help create.)

The men will get training, paid for by Emerson, customized by industry. Each will also get support to continue his education, whether that means a GED or college degree. “We recognize that not every guy is going to make it through [the program], not every guy is ready,” says Duncan. “But those who do, their actions speak loud.”

The way Duncan envisions it, the program will evolve based on feedback from those involved. One component that the Cook County inmates already persuaded him to add: parenting guidance, because, as he estimates, three-quarters of his target group have kids. 

Duncan began approaching employers this summer, focusing initially on those in health care, retail, advanced manufacturing, and logistics. He won’t say exactly how many he’s hit up, just “not a ton.” And he acknowledges that it’s not an easy sell: Many of these executives think it’s risky to hire men who in many cases have criminal records, sometimes violent ones, and no high school diplomas. Only one company, Echo Global Logistics in River North, has committed to the program so far. (Though Duncan says he hasn’t gotten any flat-out rejections, either.)

When he talks to employers, Duncan emphasizes that the program is not about handing out jobs as a feel-good move. For it to work, he says, companies must have a real employment need and be open to nontraditional workers. “It’s definitely a different talent pool,” Duncan says. “But they have tremendous heart, different skills, and they’ve been through a lot. They want to make a change in life.” 

Echo, a freight- transportation management company, hires about 40 employees a month but struggles to find and retain good ones, says CEO Doug Waggoner: “In our industry we have more turnover than we would like. I wonder if people who appreciate the job more might be more inclined to stay longer.”

It turns out that Echo is a natural fit for Emerson’s program. Salaries start at around $40,000, and, as Duncan notes, the skills involved in freight brokerage—a strong work ethic, good customer service, the ability to organize a complex network—aren’t too far off from what drug dealers hone on the street.

Echo plans to hire 20 employees through Emerson sometime in 2017. But many of the details still need to be worked out. For one thing, there’s the matter of Echo’s employment policy: Until now, the company has banned convicted felons. “That’s one of the things we have to reconcile,” Waggoner acknowledges. 

Twenty-eight men in matching black T-shirts emblazoned with “Create Your Economic Destiny” (that’s CRED, if you disregard “your”) sit around tables on the fourth floor of the U.S. Bank building in Pullman. A hand-drawn poster shows a staircase, with the lowest step labeled “Where I am now” and the highest, “Where I want to be!!!” Plastered across the walls are large sheets of paper, each with a man’s name and a collection of Post-it notes extolling his good qualities, be they “100% real” or “kool.”

“You’ve got to set up some habits that will get you where you want to be!” Craig Nash, who works with Emerson as a “community change leader,” bellows at the men. He’s one of the trainers in Duncan’s pilot program, a yearlong initiative that began in early September with three weeks of instruction. “If you’re broke at the end of the month, that might send you back to certain habits.” Today he’s teaching these men how to budget the $15 an hour they’re getting, primarily from Emerson, while learning to demolish houses as part of the Chicago Neighborhood Initiatives’ Pullman revitalization project. (CNI is contributing $50,000 to the pilot from a grant it received.)

Learning to knock down buildings will come in another week or so. For now, the topic is why these men should pack a meal every day. “If you’re spending $10 a day on lunch, that’s $50 a week,” Nash explains to them. “What could you do with $50? We’re trying to help you be realistic.”

It’s break time, and Nash reminds the men to be polite if they go downstairs to use the bathroom or get some fresh air. Then he steps behind a turntable and starts blasting the DJ Snake and Lil Jon song “Turn Down for What.” Duncan lopes around the room in a charcoal-gray polo, also with the CRED logo, carrying a plastic water bottle and observing the men’s interactions.

Nash, along with Curtis Toler, whom Duncan recruited from the antiviolence group CeaseFire, spent the summer handpicking this first cohort by knocking on doors on the South and West Sides, meeting with community organizations, and getting referrals for soon-to-be-released inmates. They interviewed about a hundred men—all with criminal records—to find those who seemed most ready to move on to another kind of life.

And these men do seem ready: On the first day, all but one showed up on time. One even arrived 90 minutes early because he wanted to help set up. On day 3, another wore a shirt and tie instead of the standard-issue black tee. “I wanted to dress like that for a long time, but I needed a purpose,” he explains. 

There have been challenges, too. Thirty-two men were originally selected for the program, but four dropped out by the end of the first week. There was a verbal scuffle early on between two participants, but they’ve gotten past it. Two others had once shot at each other over an ongoing beef. “They were literally trying to kill each other,” Duncan says. But by being in the training class together, he points out, the men have begun to see one another less as targets and more as fellow humans. Says one participant: “If we didn’t meet each other here, we might see each other on the street and give the side-eye. But we’re all in the same boat.” 

This program isn’t just about developing job skills; it’s also about addressing the trauma these men have experienced on the streets and teaching them better ways to communicate with each other and, eventually, their employers. The tactics are fluid, too. Nash and Toler noticed on the first day that some participants became agitated during a writing exercise—it was too much like being in a classroom—so role-playing was swapped in. “We let them know we’re not judging,” Nash says. “We try not to be too preachy.”

During lunch, Duncan leads a discussion about everything from Illinois’s gun laws to black-on-black violence. (“It might sound funny to hear a guy who looks like me say this—” Duncan starts when a man cuts him off: “Don’t call yourself a white guy!”) Duncan especially wants to know from the men how the first week went. “We all crawling right now,” one says. “This man is going to teach us how to walk.”

If the training program proves successful, Emerson is eyeing spots in North Lawndale, Austin, and Englewood for similar courses. But even before the Pullman pilot began, Duncan got Emerson involved in the city’s youth employment program One Summer Chicago, focusing on One Summer Plus, an offshoot that targets high-risk students. This year, One Summer Chicago planned to employ 25,000 high schoolers, many of whom would be earning a paycheck for the first time, to do things like help renovate schools. For its first official initiative with Duncan, Emerson funded an additional 4,700 slots.

Evidence shows that such jobs make a quantifiable difference. In a 2014 study of One Summer Plus, the University of Chicago Crime Lab found that the number of arrests for violent crimes among participants was 43 percent less than for a control group without jobs—and not just during the summer: Arrests among participants stayed down for 16 months. 

CPS’s chief of security, Jadine Chou, who helped coordinate the school renovations, says that to her knowledge not one of the nearly 300 students who participated in that portion of the program committed a violent crime this summer. She knows for a fact that none of them were victims. “They respond vocally that this is helping them to be safe,” Chou says. “They don’t just see it as a paycheck. They understand that by having something to do, that keeps them from doing things that wouldn’t be as productive.”

Duncan knows all too well what’s at stake. During the time he was CEO of CPS, from 2001 to 2008, a student was shot to death off campus every two weeks, on average. “This was by far the hardest issue I dealt with,” he says. He can still remember many of the students’ names and the details of their deaths. One was Starkesia Reed. In 2006, a stray bullet fired from an AK-47 a hundred yards away killed the 14-year-old in her house as she was getting ready for school. This summer, Duncan saw her mother, Denise Reed, on a CTA bus. Memories flooded back of walking into her living room to offer his condolences, though it was Reed who ended up comforting Duncan.

“I guess my point is, it’s very, very personal,” he says. “I wish we didn’t have to work on this. I wish it weren’t so bad right now. But it’s reality.”

He continues: “I feel just a huge sense of urgency. As tough as it is emotionally to deal with, whatever burden or weight I’m carrying, it’s a thousandth of what these kids are dealing with every day. And if I can’t handle my little piece, how can I help them?”

And here, in his office overlooking Michigan Avenue, he begins to cry.